Water → 2-(Tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (+/−)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in DCM (0.09 M) was added triethyl amine (1.5 equiv.). The reaction mixture was cooled to 0° C. and MsCl (1.2 equiv.) was added to the reaction and stirred for 3 hours. To the solution was added water, the organic phase was dried with sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate as a white foam in 65% yield. LC/MS=428.2 (M+H), Rt=0.88 min.

Provenance & Evidence